A parking management system and methods of operation are disclosed. In one variation, a computer-implemented method comprises receiving positional data concerning a listing location from a listing client device; establishing a radius boundary based on the positional data; filtering one or more databases using the radius boundary to determine an amount of parking spaces listed and the amount of parking spaces reserved within a preset time period; calculating a location-specific transaction rate using the amount of parking spaces listed, the amount of parking spaces reserved, and the preset time period; determining a recommended listing price based on the location-specific transaction rate; and transmitting the recommended listing price to the listing client device.